Propionyl chloride → HCID 21949640, compound

HRID 2215256Notes

Reaction equation

HRID 2215256 reaction equation
[C:1](Cl)(=O)[CH2:2]C.[C:6]([C:10]1[O:11][C:12]([CH2:36]C)=[C:13]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[C:27]3[CH:26]=[CH:25]S[C:23]=3[C:22]([CH2:28][CH:29]([O:33][CH2:34][CH3:35])[C:30]([OH:32])=[O:31])=[CH:21][CH:20]=2)[N:14]=1)(C)([CH3:8])C>O=[Os](=O)(=O)=O.[BH4-].[Na+]>[CH2:34]([O:33][CH:29]([CH2:28][C:22]1[C:23]2[C:27](=[CH:26][CH:25]=[CH:1][CH:2]=2)[C:19]([O:18][CH2:17][CH2:16][CH2:15][C:13]2[N:14]=[C:10]([CH2:6][CH3:8])[O:11][C:12]=2[CH3:36])=[CH:20][CH:21]=1)[C:30]([OH:32])=[O:31])[CH3:35]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 21949615HCID 21949615, compound

Product 1

HCID 21949640HCID 21949640, compound

Reagents, catalysts & solvents 1

HCID 131725947HCID 131725947, compoundCatalyst

Procedure

was prepared in analogy to example 59, but starting the reaction sequence with propionyl chloride instead of isobutyryl chloride, and elaborating the terminal double bond via hydroboration with 9-BBN (as described in example 53) into a primary hydroxy group instead of oxidative cleavage with OsO4/NaBH4, as off-white solid of mp. 113–17°.

Workup

  1. customwas prepared in analogy to example 59

Sources & evidence

ORD record
ord-8983b5a2746c441f9f6b0643d8b17033
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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